


Practice Makes Perfect

by fanfic814



Category: Supernatural
Genre: Anal Fingering, Anal Sex, Dry Humping, Dry Orgasm, Frottage, M/M, Multiple Orgasms, Pillow Talk, Post-Coital Cuddling, Prostate Milking, Shameless Smut, Sibling Incest, Sibling Love
Language: English
Status: Completed
Published: 2015-08-19
Updated: 2015-08-19
Packaged: 2018-04-15 12:27:57
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,811
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4606746
Author URL: https://archiveofourown.org/users/fanfic814/pseuds/fanfic814
Summary: <blockquote class="userstuff">
              <p>Dean's gonna admit his feelings for Cas one way or another... </p><p>Wincest-y fooling around follows.</p>
            </blockquote>





	Practice Makes Perfect

"I'm sorry sir.  We only have one room available and it's the honeymoon suite." the hotel receptionist said.

"What's in the honeymoon suite...Cheryl?" Dean asked, checking her nametag.

"It's only one bed.  But it's king-size and it does have a heart-shaped Jacuzzi!" she said cheerfully.

Dean looked at Sam and sighed.  "You sure you didn't see a motel around here?"

"I'm sorry, sir," Cheryl cut in.  "You won't find a motel close by.  You may have noticed we're kind of in the middle of nowhere.  The next town with a motel is almost 60 miles from here."

"So what do you want to do?" Sam asked.

"I'm freakin' tired, Sammy.  Can we just share the bed tonight?  Are you cool with that?"

"Yeah.  Sure.  We'll manage," Sam agreed.

"Okay!  You also get a complimentary bottle of champagne and chocolate-covered strawberries with the honeymoon suite!  I'll have room service send that right up to you.  Your room number is 41.  Check out is at noon.  If you need anything, just dial '9' to reach me.  Enjoy your stay!"   Cheryl shoved some key cards at them and they made their way up to their room.

"Movin' up in the world, Sammy.  An actual hotel."

Sam rolled his eyes.  "This isn't exactly the Ritz-Carlton.  Let's see what $79 a night gets you nowadays."

"Wow," Dean started as he opened the door.  "This is uh... somethin' else."

"Skeevy 70's decor, red heart-shaped Jacuzzi in the bathroom... I feel like I'm in a bad porno," Sam said, laughing out loud

Dean shook his head and set his bag down on the bed and began to dig through it, looking for a change of clothes. "Whatever.  I'm so tired, I don't even care.  Gravedigging wipes me out."

Before Sam could respond there was a knock at the door. "Just bringing your champagne and strawberries, sir!" the room service attendant said cheerfully.  "Enjoy, you lovebirds!"

Sam took the items and thanked him, and he snorted as he put the items in the bar fridge.  "So... we have  _this_."

"It's the honeymoon we never wanted, Sammy!" Dean said cheerfully as stripped down to his underwear and pulled on a comfy old band tee.

"Lucky us."  Sam stripped off his shirt, jeans, and socks, leaving only his boxers.  He climbed into bed and slipped under the covers.  "This is actually pretty comfy."

"S'about to get comfier," Dean said, pulling back the covers on his side and getting into bed.  He reached over and clicked off the light.  "C'mere, Sasquach," he said, pulling Sam in close to his chest.

"Woah.  Been awhile since we did this," Sam mumbled, wrapping an arm around Dean's waist.

"Too long," Dean agreed.  When they were kids, snuggling close for comfort seemed like the most natural thing in the world.  Now that they were adults, it usually made Dean feel guilty. Especially since on rare occasion their snuggling had turned into handjobs and dry humping.  He'd tried to justify it so many times -  It wasn't like their lives left any room for sex or relationships.  You couldn't expect a guy to never have any physical intimacy, right?  Tonight, none of that mattered.  He was tired, stressed out, and just wanted the comfort of his brother.

"Night, Sammy."

"Night, Dean," Sam said, nuzzling into Dean's collarbone.

Within minutes, Sam was nibbling and kissing at that collarbone, as Dean halfheartedly batted him away. "M'tired, remember, Sammy?"

"C'mon, Dean," Sam coaxed, kissing his neck.  "Please?  You can stay awake a little longer.  It's been so long.  I need... you know."

Dean laughed.  "Fine, if you wanna do all the work. I'm exhausted, man."

"Fine with me," Sam said, rolling Dean onto his back and positioning himself between his legs. He lay on top of him gently and started moving his hips, slowly building up the friction between them.

Dean groaned.  "Okay, I have to admit this feels really good.  Fuck, it's been awhile since I even jerked off.  Been so stressed..."

"Me too," Sam grunted, kissing him roughly as he sped up.

"When was the last time you had sex, Sam?" Dean asked breathlessly.

"Fuck," Sam sighed.  "Ruby?  Three years ago?"

"Yeah.  'bout that long for me too. We should really do something about that."

Sam paused, giving him a strange look.  "You don't mean..."

"No!  Fuck, Sam.  I just meant we need to get laid more often," he said, "Now keep movin'," Dean laughed, tapping at Sam's hip.

"Well," Sam continued grinding on him and grunted, "If you wanna get laid, I know someone who'd fuck you in a heartbeat.  Like, I could call him here and... you know."

"Don't even say it, Sammy" Dean grumbled, forcing his hips harder against Sam.

"Fuck, Dean.  You're so into him it's ridiculous," Sam said sinking his teeth into his shoulder, which made Dean moan loudly.

"Shut up dude, I'm into women, you know that," Dean said.

"Doesn't mean you're not into guys too," Sam teaased, rutting into him.

"I'm not into guys, Sam!" Dean roared.

Sam snorted.  "Yeah, and what we're doing is  _totally_  heterosexual right now, Dean."

"Oh fuck you," Dean spat.  "Get off of me."  Dean pushed forward, trying to muscle his way out from under him, but Sam's enormous frame kept him pinned to the bed.

"Uh uh," Sam grinned. "Not 'til you admit it," he laughed gleefully.  He stopped rutting and muscled him down, pinning his arms over his head.  Sam suddenly had flashbacks of Dean holding him down and giving him noogies until he'd admitted to something he'd done as a kid and it made him laugh.  "Dean, Dean, Dean...  Okay, so you're not into 'guys', but you're clearly into Cas.  He's an angel so I guess he doesn't count, huh?"

"Just fuck off already, Sam!" Dean yelled, shoving against him, to no avail.

"I should call Cas down here so he can hear when you give in and finally admit it," Sam teased.

"Sam, don't you dare..." Dean growled.

"Alright, alright.  Calm down. Take a deep breath. I'm just playin' with you, Dean."  Sam slowly began rutting into him again.  "C'mon take it out on me this way," he teased, finally releasing Dean's arms.

Dean surged forward, violently flipping Sam onto his back and jerking Sam's boxers off in one smooth motion.

"Fuck, Dean!" Sam gasped.

Dean stood up and kicked his off too.  "You wanna fuckin' play, then we'll play, Sammy," he snarled, pouncing on the bed.  He pried Sam's legs apart and lay between them and began rubbing their cocks against each other again.  Sam trembled excitedly as the warm sensation of skin on skin pervaded his senses.  They were both slick and wet with precome already and they slid against each other almost effortlessly.

Dean leaned in for a rough kiss, and Sam whimpered a bit beneath the onslaught of Dean's tongue pillaging his mouth and the teeth tugging and grazing at his lips.  "S'wrong, Sammy?  You were the one who wanted to get off tonight."

"Nothing.  I like it.  Just never seen you like this," he gasped.

"Well you said you like it rough, so..."  Dean reached over to the nightstand and pulled out a bottle of lube.  He pulled away and slicked a glob of lube over his cock.

"Dean.  What are you doing?"  Sam asked, his eyes suddenly wide.

"What's it look like?" Dean grumbled.

Sam laughed.  "Looks to me like you're trying to fuck me."

Dean raised an eyebrow questioningly, waiting for Sam to back down.

"Go for it," Sam said nonchalantly.  "Long as you ease me into it, I'm down."

"Seriously?" Dean asked, suddenly shaken from his anger.  He didn't really expect Sam to be so willing, he'd just planned on teasing him a little until he whined for Dean to leave him alone.

"Alright," Dean said, determined to call his bluff. "Let's do this."  He slid a lube-slicked finger slowly into Sam's hole, half-expecting Sam to tackle him, but he didn't.

"Mmm," Sam mumbled.  "Keep going.  More."

Dean shook his head, sure Sam would crack this time as he inched another finger inside him.

Sam squirmed and groaned a little but he seemed fine with it. "Move your middle finger like this," he instructed, making a 'come here' gesture with his finger.  "Feel that little bump?  Yeah.  Keep rubbing"

Dean did and Sam mewled like a baby.  "Mmm, yeah. Right there," he moaned.

"Fuck, Sam," Dean said breathlessly. "You're actually enjoying this," he said incredulously.

Sam erupted into laughter.  "Umm yeah, why wouldn't I?"

"You ever uh..." Dean started, unsure of how to ask.

"Been with a guy?  Yeah.  Few times in college.  Been a long time though.  Plus Jess used to fuck me with a strap-on sometimes"  He moaned again suddenly and Dean looked down, realizing he was still rubbing against his prostate.  He stopped moving for a minute.

"And you uh... liked it?"  Dean asked curiously.

"Fuck yeah.   Why not?  Keep going," he pleaded.

Dean furrowed his brow and pressed into Sam with a third finger.  Sam gritted his teeth and grunted as it slid deep inside next to the others. "Fuck!" he yelled.  "Oh god.  Now move a little.  In and out," he begged.  Dean did.  "Ohhh yeah," he sighed happily.  "Spread your fingers just a little bit... oh fuck!  Nnngh," he babbled incoherently.  "Rub again..."

Dean sat there for a good fifteen minutes, massaging into him.  He was absolutely mesmerized, watching Sam writhe on his fingers, feeling utterly perplexed. He didn't know Sam had done this before.  He didn't expect Sam to  _like_  doing this.  He'd only intended to hold him down and tease him until Sam begged him to get off of him.  He  _really_  didn't expect Sam to beg for... well,  _this_.

"So you gonna fuck me or you gonna chicken out?" Sam teased. After so many years, Sam still knew how to bring out Dean's competitive streak.

Dean slid his fingers out as Sam hissed in protest and he tentatively pressed his dick against Sam's hole.  "You sure about this, Sammy?"

"Bring it," Sam smirked.

Dean slowly sunk into him, watching Sam's eyes glaze over as he moaned.

"Howzat feel, Dean?" Sam slurred.

"Oh god. That's nice,  Tight.  Warm.  Fuck, it's kind of amazing," Dean laughed nervously.

"Not bad on this end either," Sam grinned.  "Now move," he commanded, slapping Dean's ass.

"Fuck, Sam!" Dean yelped, but began moving slowly on top of him.

"Mmm. Speed up a little Dean, you're not gonna break me."   Dean increased his speed incrementally, and Sam sighed in frustration.  "C'mon, Dean, give it to me!"

Dean gritted his teeth and began thrusting into him.

"Yeah, that's it," Sam grinned, letting his fingers play over Dean's right nipple as Dean whimpered. "Fuck me like you're still pissed at me for mentioning Cas," he teased.

Dean rolled his eyes and pressed in close to him, biting into his shoulder hard as he thrust.

"Fuck, now that's what I'm talkin' about!" Sam exclaimed. Sam glided his hands up and down Dean's back, urging him on.  Every so often he'd grip his fingers into Dean's ass and thrust back, making Dean determined to thrust that much harder.

"Sammy,  I'm close, man.  Should I uh..."

"Just keep going," Sam grunted.

Dean nodded and slammed into him even harder, Sam was clenching around him so tightly, Dean thought he might pass out.  Sam had tightened his grip around him, pulling him tightly against his chest as he began practically convulsing beneath him.  For a second, Dean was overwhelmed just watching him - face flushed bright red, moaning and... he was fucking  _drooling,_ for Christ sake. Sam's legs flailed wildly and suddenly Dean had to fight to stay on top of him.  A few short thrusts later and Dean followed him down.

"Sammy," he whimpered gripping onto him and letting the little shivers of pleasure wrack his body.

Sam screamed - fucking  _screamed_  - and lay there twitching as Dean collapsed against him.

Dean was content to just bask in the afterglow for a few minutes but Sam kept twitching and moaning, even after Dean's now-flaccid cock had slid out of him. It was a bit disconcerting.

"Sammy?  You okay?" Dean asked softly.

Sam nodded, moaning again. "I need... handjob.  Please?" he gasped.

Dean furrowed his brow in confusion and rolled off of him.  Sam was still mostly hard and twitching.  "You didn't...?" Dean started.

"Come?  No.  Just.  Please." Sam begged.

Dean spit into his hand and pumped Sam's cock once, twice, three times and he came, screaming again and spurting violently into Dean's hand. His body finally relaxed a bit and Dean lay down next to him, placing a hand on his heaving chest.  He gave him a few minutes to catch his breath and then launched into the onslaught of questions.

"What the  _fuck_  was that?" he exclaimed.

Sam chuckled weakly. "Multiple orgasms?"  he grinned.

"That's not possible!  And you didn't..."

Sam nodded, another twitch shaking his body. "Oh my repressed brother," he smirked. "Totally possible.  Proper prostate stimulation equals multiple dry orgasms."

Dean squinted at him skeptically. "What fun is a dry orgasm?"

Sam laughed again. "All the fun, none of the mess?  Way more intense?  Fun in that you can have multiples?   Seriously.  I had sixteen in an hour once before I was foaming at the mouth and finally had to jerk off to relieve the pressure."

Dean shook his head quizzically.  "You were drooling pretty good a few minutes ago there, Rover."

"Yeah well.  It's pretty intense.  Hey, can you um, grab me a towel or something?  I'm kinda covered in jizz here," Sam grimaced.

Dean laughed and trotted off to the bathroom, returning with a hand towel.  Sam wiped his stomach and thighs off and handed the towel to Dean. "Gimme a hand?" he wrinkled his nose, bending his knees and spreading his legs.

"Do I have to?" Dean whined.

"That's your come dripping out of my ass if you forgot, so yes," Sam grumbled.

"Alright, alright," Dean agreed.  He berated himself as he gawked at Sam's still slightly stretched hole, dripping a trail of his come.  He should not be so turned on by this.  He wiped him down as best he could, as Sam jerked and giggled at how sensitive he still was.  "There. All clean."

"Thanks.  Come here," Sam said, urging him to snuggle into his side. Dean sunk into the bed with his head on Sam's shoulder, wrapping an arm around his waist.  "You alright?" Sam asked.

"Fine, why?"

"Just makin' sure. Wanna make sure you're not traumatized," he teased.

Dean stretched and yawned.  "Maybe if I were on your end of it," he grinned. "What's it feel like?" he asked sleepily. "Does it hurt?"

"I wouldn't say it hurts.  It's a little uncomfortable at first.  And then it just feels like a... I don't know, a fullness. A fullness you never knew you needed there," he laughed. "And there are lots of sensitive little nerve endings, so it feels nice.  Then once you start going to town on the prostate... I've been trying this thing where if you don't touch yourself you don't come and... uh, if you don't come you can have a few dry orgasms first.  And fuck, they're the most mind-blowing orgasms ever. Seriously, I black out a little, see stars, drool, scream. It's kind of embarrassing, really, but so damn amazing I don't care."

"Interesting," Dean mumbled.

"Took some practice. But worth it," he mumbled.   "Dean?" he suddenly asked. "Is it the sex thing you're scared about?"

"What?  What are you talking about?"

Sam shifted onto his side, propping his head on his elbow.  "I mean, just the way you were talking earlier.  I mean..." he sighed.  "I mean, with Cas."

Dean flushed a bright crimson color,  "What?  I..."

"That's what I thought," Sam laughed.

Dean rolled over onto his side so he didn't have to face him, but Sam quickly slid in behind him and spooned him. "Want to uh... want to try it?"

"Can't I just lie here and enjoy the post-orgasm bliss without talking about Cas?" he whined..

"C'mon, Dean," Sam whispered in his ear. "Don't freak out. I'll help you."

"I... I don't think I can do it, Sam," Dean whimpered.

"Never know if you don't try.  Come on.  One finger.  Nothing else unless you're ready."

"Fuck," Dean groaned.  "Fine.  One finger."

Sam bit his lip and grinned.  "Good.  Lie on your back and relax," he said, reaching for the lube.

Dean took a deep breath and flipped onto his back, noting that his dick was already half-interested for some reason.

"Spread your legs." Sam took his time, lubing up his fingers and then smeared a glob of lube around Dean's hole as he squirmed nervously.

"C'mon, Sam, just get it over with," he grumbled.

"Get it over with?  No, no.  Can't rush this.  Trust me.  I'm gonna take my time. Let you see how good it is," Sam laughed, rubbing circles around his hole and watching him twitch until Dean was practically begging.  "Deep breath now.  Relax," he said softly.   He prodded lightly at him with the pad of his index finger as Dean jumped and wiggled.  "Hey.  Calm," Sam reminded him, placing a hand on his stomach. Sam pressed into him with a few short, fast strokes in and out, just dipping the first knuckle in, and then he shoved in as far as he could.

Dean gasped loudly, nearly hyperventilating for a second.

"So dramatic," Sam teased.  "Breathe, Dean. It's in. You're fine."  He slowly started moving the finger in and out, then in tiny circles as Dean whimpered.  He watched Dean's eyes, pushing him right to his limit without sending him over.

"Feels weird, Sammy," Dean muttered. "I don't know about it."

"Doesn't hurt though, right?"

"I guess not.  Uncomfortable," he groaned.

"Just get used to it for a minute," Sam said softly. "Take your mind off it," he teased, leaning in to kiss him.  Dean wrapped his arms around him desperately.  Sam crooked his finger and prodded gently at Dean's prostate.  While it didn't feel like much of anything at first, Dean was shocked when it suddenly started feeling  _good_.  "That's not so bad right there," he moaned

"Yeah," Sam nodded.  "Can I slip another finger in you?" he whispered.

"I don't know, Sammy," he whined.  "You can try. Maybe."

Sam pressed into him again, slipping the second finger in without much warning this time.  Dean yelled and tried to squirm away from it.

"Dean," Sam said firmly. "Stay."  He looked down at Dean's big green eyes, swimming with tears, his nostrils flaring slightly with his gasping breath.  "Promise you're gonna be fine," he said softly.  Dean closed his eyes and stilled, taking a deep breath.

"That's it, really.  My fingers are pretty big, so if you can handle this, you can handle...  y'know."  He rotated his wrist a few times and spread his fingers just a bit, then started rubbing methodically at that little bump that made Dean jump and tremble.  Each time Dean tried to touch himself, Sam would smack his hand away.  Dean was twitching, rocking into him every so often, his mouth gaped open like he was about to say something but couldn't.  So Sam just kept massaging him, ten, fifteen, twenty minutes.  Every so often, his eyes would roll back and he would scream and thrash hard, fisting his hands into the sheets.  Thirty minutes and Dean was utterly fucked out, but he hadn't yet come.  His vision was hazy and he couldn't think straight.  Much to his dismay, he was drooling, just as he had made fun of Sam for doing.

"Sammy," he squeaked. "I can't... no more. Need... let me... come."

"Okay, okay," Sam whispered, pulling away then turning his attention to Dean's red and leaking cock.  He stroked gently for a minute or two and Dean yelled as he exploded into Sam's fist, painting Sam's hair and half the motel wall.

Sam laughed and reached for the towel, wiping at his hair and hand before trying to wipe Dean clean.

Dean protested, whimpering, "S...sensitive," so Sam gave up and lay down next to him.

"You okay?" he asked softly.

"I... I don't know what I am," Dean blubbered. "Kinda terrified at how much I liked that."

"What's to be terrified about?" Sam asked, pulling him into his arms. "Breathe, Dean.  Jesus, you're wheezing."

Dean was quiet, taking some slow, deep breaths, trying hard to slow his panting.  "Fuck, Sam, all I wanted to do was snuggle and sleep tonight."

Sam laughed. "Yeah, well you changed your mind pretty quick. Way more intense, right?"

Dean nodded.  " _Way_  more."

"So takin' it up the ass isn't so scary huh?" Sam teased.

"Still a little scary," Dean mumbled. "Receiving is a lot more emotional than giving.  I've fucked dozens of women and never once felt vulnerable like that.  Guess I should be a little more thoughtful toward the girls I sleep with, huh?"

"Couldn't hurt," Sam agreed, lazily running fingers through Dean's hair.

"I'm gonna feel real fuckin' guilty about this in the morning," Dean sighed.

"Oh Dean, stop it.  We've been fooling around since I was eighteen. So we... went a little further this time," he fumbled for words.

"A _little_?"

"So what, Dean?  We can't have normal lives.   You know it's just you and me out there.  And since when have we ever cared about what other people think is normal?"

Dean sighed. "I know.  Still feel weird about it sometimes."

"I know. Weird's all we know, Dean."

"Ain't it the truth, Sammy?"

They lay there in an awkward silence for a few minutes just holding onto one another before Dean finally spoke again.

"So Jess used to fuck you in the ass, huh?"  Dean laughed quietly. "Never knew she was so kinky."

"Oh god, you have no idea.  She was into some crazy BDSM stuff. Restraints, spanking, punishment... Good times," Sam smiled sadly.

"I am learning  _way_  more about you tonight than I ever needed to know, Sam," Dean yawned.

Sam laughed. "Life's short, Dean. Try everything.  Sometimes you find out you fuckin' love it."

Dean nodded weakly. "I'm a slow learner, Sam."

"That's okay," he said softly. "So... about Cas."

"God, Sammy!" Dean groaned.

"C'mon, Dean," Sam grinned. "Less scared now at least?"

Dean sighed deeply.  "Yes."

"Good.  He's a good guy.  He loves you, you know."

"I know," Dean tightened his grip around Sam's waist.  "I'll call him tomorrow," he sighed, "and I'll do...  _something_  about it."  
  
Sam squeezed him a little tighter and ruffled his hair. "You tired?"  
  
"Fucking exhausted," Dean mumbled.   
  
"Get some sleep," Sam laughed. "I'll wake you early to soak in that cheesy Jacuzzi.  You'll be sore from all that thrashing around."  
  
Dean nodded drowsily.  "Love you, Sammy."  
  
"Love you too, Dean."


End file.
